My plan until this year was to sell up the stock and the holding, buy somewhere in a tourist area (Trossachs or East Neuk villages) that I'd actually like to stay in occasionally but mainly let out through an agent as a holiday let all summer and a 6 month shorthold tenancy in winters IF I didn't want or need it myself. I'd also have the option to stay in it any unbooked weeks obviously at other times but my thought was that once released from the ties of responsibility and with a property bought outright in Scotland, the remainder would be to live off in some form, be it another (BTL mortgaged) property (preferred option at the time) or other investments.
I looked at what I thought I wanted, a solid investment and home base in Scotland plus freedom to go travelling globally doing whatever I could/wanted/had chance to do. Volunteering placements that don't charge immense fees but provide basic accommodation, long distance walks/treks eg the Camino in Spain, visiting relatives and friends I've said no to for years due to "feeding the animals" or "work" or both. But I wanted freedom without a hassle hence the agent and hence not buying abroad, despite some of the wishlist being travel abroad.
I thought if I went different places each year, experienced the joys of travel, then at some point I'd want to sit for a few months in one place and write or do crafts or rest, but not leave it empty so make it the business paying UK tax and my 6 month official residence too. I'd also not want to lose access to NHS as I get older, nor my resident status. Making a mistake with the overseas stuff could be costly in more than financial sense, limited English speaking neighbours can make life tough if you don't get on, selling up is harder than buying, healthcare and other government systems being unfamiliar aswell as payments/insurances etc. To make life easier, don't add new bureaucracies in foreign languages, that was my primary thought!
I haven't sold the stock obviously, market isn't right but I'm still reducing the ponies as steadily as I can find the right kind of buyer at a decent price and anything I breed now I will advertise, tho I reckon I may still have to find "fosterhomes" for some of the older/crocky/favourite ponies while I'm away for the foreseeable at least, I can't sell my OAPs who might go this winter or last another 10.. but the capital and reduced costs and time out would hopefully pay a minimum grazing fee for summer absences if nothing else. And I am also thinking rent the holding out for a trial run of "freedom" before I sell up completely, in case all I needed was a break to get fit and well again..
Not your scenario but maybe there are a couple useful points in there somewhere!